The Sexual Conquests of Dean Winchester
by Wofl
Summary: or 12 Steps to Becoming a Sex God The early years. Wincest. Dean x multiple OFCs. Mature. Angst. Schmoop. Drabbles.


_-January-_

Dean is thirteen today, and his father says nothing at breakfast. Dean tries not to be disappointed. It's not like it's the first year this has happened.

He walks to school, holding Sammy's hand, and during recess, the brunette that sits just in front of him during math pushes him up against the bars of the jungle gym and kisses him breathless.

Heather. Her name is Heather.

She tells him happy birthday, and Dean wonders how she knew, but nods anyway when she asks him to meet her after school. It's not like he has any other plans.

They go bowling and Dean spends the afternoon wondering whether or not this counts as a date. He supposes it does when she pulls him behind the soda machine and kisses him again. He kisses back this time, but he's clumsy and nervous and the man that fixes the pin stacking machines when they get jammed clears his throat and gives them a nasty look. They break apart with stammered apologies and go back to their game.

Dean bowls the best game of his life, that day, and still loses by ten points.

_-February_-

His father gives him the Impala when he's fifteen. He's still too young to have his license, but he's been driving since he was ten, and, well, John needs something with better gas mileage.

He drives to school now. And suddenly, he has a lot more attention from girls that had previously probably not known he even existed. He takes a few of them out, smiles when they fawn over him and his kickass car, even gets to second base with a few of them, but that's as far as he goes.

It isn't until he meets Claire that he lets anything more than that happen. She's a junior, with big lips and fire-engine red curls framing her pale face and miles upon miles of legs. He takes her parking up at the local spot, one night, and they find a quick remedy to the cold of the season.

She's _hot_ and she's got Dean fired up in ways he's never been before. His pants are tight in a way that borders on uncomfortable and Claire lets him slip his hands up underneath her shirt. When she asks if he has a condom, he tells her he does, but that he's never done this before.

She just grins and tells him she's going to take care of him. And take care of him she does.

Later, after he drops her off at her place, he pats the dashboard of the Impala affectionately, in a loopy sort of thank-you. He supposes this makes his ownership officially official or something like that.

There's a whole new world of possibilities spread out before Dean. Sitting behind the wheel of the Impala, he can't think of any way he'd rather pursue them.

-_March_-

The end of the month approaches, and in Baltimore, the sun melts the snow and Dean melts girls' hearts.

With experience comes confidence, and since last year, Dean's managed to obtain plenty of both. They've been at their new school just over a week now and Dean already has the numbers of five different girls pinned up on the inside of his locker. I's dotted with hearts, loopy scrawled letters spelling out the names and digits; the sight of them gives him something to smile about between the classes he's beginning to find harder and harder to care about.

It's customary, for him, to be hanging around in the parking lot after the final bell rings. Sammy usually stays a few extra minutes in the library, doing something or other, and Dean doesn't mind waiting. It's time well spent, usually with his tongue fishing around in some easy girl's mouth. He compliments them, teases them into letting his fingers brush against parts that still send a thrill straight to his cock.

All the awkward shyness is gone, and in its place is the quick learner that Dean's always been. He experiments with new methods, trying them out on various girls, develops theories and puts them to the test. His mind gleans out the details, picks up and stores away what works and what gets his face slapped. Girls like compliments, they like smooth and easy, confident and maybe just a little bit bad.

Dean can be all that.

But when Sammy comes out, most likely accompanied by a stack of books, it doesn't matter who the girl is, it's always back to business then. Ever since his father bequeathed the Impala to him, Sammy has been his faithful shotgun rider.

Dean swears to himself that he will never let a girl take his place. Not even the perky blonde captain of the cheerleading squad.

Luckily, Dean has the empty girl's locker room for that particular venture.

_-April-_

It's not that Dean doesn't want a steady girlfriend. In fact, he has his heart set on a mousey sort of girl that he meets in Jersey. And if not his heart, truly, at least his libido.

She's not much to look at; kinda plain, one of those sorts that blends in with a crowd, but holy hell is she a firecracker. She teaches karate after school. The day Dean watches her take out a boy twice her weight and size and makes it look _easy_ is the day he asks her out.

He learns her name is Phoebe, and it turns out, self-defense is not her only area of expertise.

When the time comes, she's the first girl that Dean is sad about having to leave behind. He vows that she will also be the last. Dean won't make that mistake twice.

_-May-_

Maggie is the most popular girl in school. With her looks, it's no surprise. She's tall and leggy and her knockers…whew. She's got raven-dark hair that falls around her shoulders and the bluest eyes Dean's ever seen.

Dean likes her because she's a challenge. She can have her pick of any guy she wants, and Dean takes it upon himself to make her choose _him_. How hard can it be? He's Dean Winchester, after all.

It only takes him a week to woo her. She falls for his leather jacket and his sneer; the one that curls the corners of his mouth up like a predatory cat. Turns out, Maggie's got a thing for the bad boys.

On the first day of the month, she cuts class with him and they find themselves out by the football field. When he shows her how to flip a knife, she drags him underneath the bleachers, practically purring. She's got her lips on Dean's mouth and her fingers on the button of his jeans. She sucks him off with obvious expertise and Dean is left breathless and grinning dopily when they finally make their way back to the school.

The next day, as Dean waits in the parking lot for Sam, she finds him and with no preamble, kisses him hard. He cops a feel and she palms him through his jeans, right there in broad daylight. It's probably the hottest thing, ever, and he loses himself to it.

She pulls away, breathing hard and looks Dean over with decidedly hungry eyes. She asks him to go to a movie with her after school. He's about to say yes - his eyes gleam at the thought of spending two hours in a dark room with her frisky hands – but then he spots Sam making his way across the lot towards him.

Dean remembers what day it is.

He tells her no, and she stalks off in a huff and Dean is disappointed because he knows he will never get another chance with this girl. When Sam climbs in the car, Dean wishes him a happy birthday and reminds himself that there are more important things.

He takes Sam to the movies instead, and, because it's his birthday, Dean lets him choose which film they see.

_-June_-

With school out for the year, they move around more. The west coast flies by in a blur, counted only by the miles that slip away beneath the Impala's worn tires and the number of spent shells that fall from their rifles, the last traces of rock salt clinging to the smoking cartridges. Washington, Oregon, California, Colorado, Nevada, New Mexico. They blaze a trail of triumph over evil, leaving unsung glory in their wake.

Somewhere along the line, Dean loses track. He follows behind his father's truck faithfully; wonders if Dad ever gets lonely during those long miles, now that Sam has taken to riding in the Impala with Dean.

He's not old enough to frequent the bars, yet. But he's seventeen now, and his father gives him a fake ID and a five minute speech. He doesn't care if Dean drinks or smokes pot, he says, as long as Dean doesn't let it fuck up a hunt. And if he ever catches Dean with anything else…well, he makes sure Dean knows he'll live to regret it.

Dean nods and swallows hard, accepting the laminated bit of paper with trembling fingers and something in his heart jumping excitedly. This is, perhaps, his father's way of letting him know he thinks of him as a man now.

That night, when he hits the bar, the bartender takes one look at Dean – travel weary and bags under his eyes - and doesn't even bother to card him. Dean is almost, _almost_ disappointed.

He meets a girl there, straw colored hair and sinfully short skirt. She's all lips, pressing them to Dean's neck in a way that lets Dean know how drunk she is. In the back of his mind, he supposes he's taking advantage of her, but he quashes his doubts with the excuse that he just as drunk as she. Certainly too drunk to care.

He fucks her in a bathroom stall. It's the first time Dean doesn't bother to learn the girl's name before he does it.

_-July-_

In Minnesota, Dean saves a girl from a cockatrice. The hunt doesn't go down as planned, and in the end, Dean faces the monster alone. It's attacking a pretty young thing, when Dean finds it; and it's lucky that she cowers in fear, covers up her eyes with her chocolate colored hair.

Making eye contact is deadly.

Dean sacrifices one of the Impala's sideveiw mirrors reluctantly, and turns the bastard to stone, but not before receiving a nice set of claw marks running up the length of his arm for his efforts. Some souvenir.

The girl is trembling, but otherwise unhurt and Dean asks her name. She says her name is Paige and she looks horrified at the blood dripping down Dean's arm. She tells him she never thought her first aid training would actually come in handy.

When Dean's arm is cleaned and bandaged and they're tucked away in the backseat of the Impala, she thanks him for saving his life. She doesn't use any words, but he gets her drift nonetheless, and soon, she's trembling for entirely different reasons.

Funny how near death experiences make a person feel so much more alive.

_-August-_

The end of the summer approaches like a plane crash. His father is frantic to get as much done as he can before the school year begins again and holds them up. The east coast falls away at breakneck speed; it feels like glaciers sloughing off into the ocean - sudden, cataclysmic.

Possessions in Vermont, water sprites in New York, pixie infestation in Delaware, chupacabras in Georgia, Will-o-Wisps in Mississippi. In between is a nightly barrage of haunted houses, torched corpses; burning flesh becomes constant lingering stench in Dean's nostrils.

Dean keeps count in his own way. Time is numbered by the lipstick stains on his shirts, the matchbooks and napkins he collects, zippers he divides and conquers. It's one nameless bar after another, fast fucks that he hardly remembers, with girls he certainly doesn't.

But they're notches on his bedpost and he displays them proudly even if he can't tell you what color her hair was or who came first. They blur into one another, undistinguishable.

The only highlight of the month is Kiki. Kinky Kiki, to be exact. She's starred in more than one porno, she tells Dean proudly, and, under the flag of sexual experimentation, he lets her tie him to the headboard in a dingy hourly-rate room above the bar.

Dean never really bought into the stereotype about Asians and crazy sex, but when she puts a gag in his mouth, spanks him raw, and leaves him hard and aching for hours, he decides that, yes, maybe there is some reason hidden in the rhyme.

That night, Dean learns all about pegging. He'll never admit to anyone that he actually enjoyed the act; least of all, himself.

_-September-_

New town, new school, fresh new faces. Dean kicks off his senior year like a dog on a hare. He sniffs out the easy girls, between classes; nails the ones that let him and works on the ones that hesitate.

Hardly two weeks into the year, he gets suspended when he's caught with his pants around his ankles and his hands unsnapping some Melody girl's bra in an empty chem. lab. Dean feels like the luckiest person alive that it happens while Dad is away on a hunt. He bribes Sam not to tell with TV privileges, later bedtimes, and driving lessons and thanks some higher power that he has the best little brother ever.

He uses his time off to court a girl named Fran. Easy girls have proved to be _too_ easy, and she's something new for Dean; shy and quiet, long blonde hair that she likes to use to hide her face. She's only a sophomore, and Dean suspects that she is a virgin.

By the time he's allowed to return to school, he's confirmed it, and made it his personal agenda to amend that status. It takes some coaxing, but after a particularly romantic date that has Dean shuddering on the inside with the sheer number of chick flick moments he's had to fake his way through, she lets him take her parking out on a scenic route.

This time, Dean is the one uttering promises of reassurance. He tells her he'll take care of her, and it's not long before her moans drown out the straining chords of Blue Oyster Cult that filter quietly from the Impala's speakers.

Virgins, he decides, are a gift from God.

_-October-_

Rain seems to follow Dean wherever he goes, these days. He supposes it fits, because if the sun were shining, he might have to pretend he is happy and he's afraid it might break him.

Twenty-three years old, and October finds Dean lonelier than he's ever been in his life. Sometimes he wakes up in the morning and forgets that Sam isn't there anymore, and it makes the reality all that much harder to bear. It's easy to drown himself; in alcohol, in pussy, in hunting. None of it is what he wants.

He knows, now, how his dad must have felt when Sammy started riding with Dean in the Impala, all those years back. It's not a comforting thought. If anything, it makes the void stretch out, bleaker than ever, at the prospect of all those silent, empty miles still to go.

The ache in his chest - the feeling of something wrong and missing – well, it sucks, but it's natural, right? Dean thinks it is; refuses to believe otherwise.

At least, he does, until the day comes when he's got a sweet pair of lips wrapped around his dick and despite her coaxing tongue, he finds he can't come. Not until he closes his eyes and imagines Sam in her place. After that, he comes so fast, it makes his head spin.

Really, it makes him too sick to consider what, exactly, this revelation means.

_-November-_

When it comes to sex, there aren't many hurdles left he hasn't jumped. His heart isn't really in it, these days; hasn't been since Sam left. But he's still young and spry and if the mood strikes him right, any sort of companionship seems nice.

Dean can't stand the cold; hates the thought of lonely beds when the weather is bitter. He convinces his father to head south. Not a difficult feat when the old man catches wind of cattle mutilations in Texas.

In Austin, Dean is invited to participate in a three-way, and thinks he'd be a fool to pass up such an opportunity.

It's completely different from the one on one sort of intimacy he's used to. There's more clumsiness, more need for care. There are more limbs to get in the way, more give and take, push and pull, general compromise. But, his teachers are good, obviously having done this before; and God, when there are two people giving you attention at once, the sensation overload is worth the extra effort.

Dean tells himself that the fact that there is only one girl involved means nothing.

And so what if the other guy is tall and lanky, with yak hair and pouty eyes? That doesn't mean anything either. Really, it doesn't.

_-December-_

Despite the impending doom that looms ever closer, Dean feels more lighthearted than he has in longer than he cares to think about.

Sam is back, and sometimes, he can't believe it. His heart feels giddy, at times, when he catches sight of the face he'd feared he'd never see again. A constant mantra making his blood flow faster, almost a low hum in his bones. _Samsamsamsamsam_.

He's not sure when it is that he stops lying to himself, but it makes his heart sink pitifully when he realizes the brotherly love he used to harbor has been replaced by a deeper and darker need. He tries to hide it, but Sam is clever, has always been too smart for his own good, and he can read Dean like an open book.

It scares Dean, how much he enjoys it the first time Sam confronts him about it and ends the argument with a fierce kiss.

It only gets worse from there.

Because once Dean has been given a taste of forbidden fruit, he wants the entire tree. Sam is the serpent and Dean falls prey to his tantalizing offer. Sam tastes like knowledge and longing and contentedness. Dean sucks him in with a vigor he hasn't felt since sex was something new to him, relishing the slick burn of heat and friction when they move as one.

If it were the only thing Dean tasted again for the rest of his life, he's fairly certain he'd be okay with that. But Sam doesn't stop there. He lets Dean have his cake and eat it too, and at the next bar they stop at, Sam finds a brunette and doesn't let on that they're brothers.

He learns her name is Caroline only because Sam tells him so. When Dean comes that night, it's wedged between the two of them, his dick buried inside her while Sam thrusts wildly into him and he couldn't have stopped the moans that escape his lips if he tried.

Yeah, it's a good day to be Dean Winchester, Sex God Extraordinaire. 


End file.
